A challenge to the efficiency of many computing environments is the volume of emails that are received, sent, and retained. Left unchecked, emails may continue to accumulate or proliferate and require discrete action by a receiver to manage them, i.e., delete or archive emails to manage usage of finite computing resources and guard performance efficiency of the resources. In order to address the challenges posed by email proliferation, some computing systems include mail retention programs that provide each email with a finite “shelf life” after which the email is deleted and/or archived. However, present mail retention approaches delete or expire email based largely on the timestamp of an email that delineates when it was received by a user. As a result, a system may retain inconsequential emails and expire or delete emails of high importance because the user failed to take active steps to prevent this deletion. A need exists for an automatic context-sensitive approach to email retention.